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Dealing With Entrepreneurial Self-Doubt
how to beat self-doubt as an entrepreneur

What a week! Flew back from Vancouver and arrived home to a complete gong show…

Prior to leaving for Vancouver, I made sure everything was in place to renovate my family home as we are preparing to sell it. All the trades were lined up and ready to go. The schedule was set in place and would work perfectly so long as it was followed…

Regrettably, trades people sometimes don’t adhere to timelines.

Our hardwood floor refinishers were supposed to be done three days before I got back, but they hadn’t even completed sanding when I returned. Not only that, but they left a corrosive bag of wood shavings on the front grass and had completely killed a third of my pristine turf… just in time for us to list our property (talk about curb appeal for a prospective buyer – it looked like a giant dog took a leak on my front yard).

Roofers contracted for my new rental property informed me the old plywood on the roof was completely rotten because of poor ventilation. So on top of the $12k bill to re-shingle, it ended up costing an additional $5k to build proper ventilation and replace the rotten plywood. Fine, I bit the necessary bullet on that one. Cost of doing business…

A day later, my new tenant informed me one of the roofers fell through the ceiling… I thought that shit only happened in the movies. Thankfully, the roofer was okay, but now there is a massive hole in the master bedroom ceiling, and I can tell my new tenant is getting frustrated with the whole situation.

On Thursday, I received a phone call from the programmers we hired for my PR company’s new web-based platform… already tens of thousands of dollars into this project, which is two months behind schedule and 30% over budget, they informed me it won’t be ready until September. Meanwhile, the old platform we are using just crashed, with many important features completely f@#%& up for good.

By week’s end we listed the family home and almost immediately drove to the developer’s office to fork over the down payment (a gut-wrenching amount of coin) and begin picking the layout of the house and finishings etc. as the builders will break ground tomorrow. The kids and wife are thrilled, which makes me happy, but building a new home is still a major time and energy drain. Throw in the fact that my cherished baby, a new tech startup I’ve been working on for two years, is heading into the most important and busy time since inception (requiring max effort and hours), and I began to get anxiety for the first time in my life last week. Nothing serious, there are people in this world in situations which make mine look like a cake walk, but nevertheless the anxiety was noticeable. Never had I experienced it before. I love being busy, and often have several projects on the go at once… that’s why it caught me off guard. You see, anxiety stems from one thing: self-doubt.

And every entrepreneur, at one point or another, must overcome this…

I began to question last week if I had taken on more than I could chew. Completely spent on Friday night, I remember thinking, ‘is this how people crash and burn out?’

Reality is, we’re never dealt more than we can handle. You just have to wake up every morning and fight. I was reminded of this when reading to one of my sons his bedtime story from The Book of Virtues (hell of a book for both children and adults by the way).

I want to share this poem by Edgar Guest with you as it served me well last week.



Can’t is the worst word that’s written or spoken;
Doing more harm here than slander and lies;
On it is many a strong spirit broken,
And with it many a good purpose dies.
It springs from the lips of the thoughtless each morning
And robs us of courage we need through the day:
It rings in our ears like a timely-sent warning
And laughs when we falter and fall by the way.

Can’t is the father of feeble endeavor,
The parent of terror and half-hearted work;
It weakens the efforts of artisans clever,
And makes of the toiler an indolent shirk.
It poisons the soul of the man with a vision,
It stifles in infancy many a plan;
It greets honest toiling with open derision
And mocks at the hopes and the dreams of a man.

Can’t is a word none should speak without blushing;
To utter it should be a symbol of shame;
Ambition and courage it daily is crushing;
It blights a man’s purpose and shortens his aim.
Despise it with all of your hatred of error;
Refuse it the lodgment it seeks in your brain;
Arm against it as a creature of terror,
And all that you dream of you some day shall gain.

Can’t is the word that is foe to ambition,
An enemy ambushed to shatter your will;
Its prey is forever the man with a mission
And bows but to courage and patience and skill.
Hate it, with hatred that’s deep and undying,
For once it is welcomed ’twill break any man;
Whatever the goal you are seeking, keep trying
And answer this demon by saying: “I can.”


Stay hungry,

Aaron Hoddinott signature


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